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19-Norandrosterone

From Wikipedia, the free encyclopedia
Chemical compound

Pharmaceutical compound
19-Norandrosterone
Clinical data
Other names3α-Hydroxy-5α-estran-17-one; 5α-Estran-3α-ol-17-one
Identifiers
  • (3R,5S,8R,9R,10S,13S,14S)-3-Hydroxy-13-methyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-17-one
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H28O2
Molar mass276.420 g·mol−1
3D model (JSmol)
  • C[C@]12CC[C@@H]3[C@H]4CC[C@H](C[C@@H]4CC[C@H]3[C@@H]1CCC2=O)O
  • InChI=1S/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h11-16,19H,2-10H2,1H3/t11-,12+,13-,14+,15+,16-,18-/m0/s1 checkY
  • Key:UOUIARGWRPHDBX-CQZDKXCPSA-N checkY
 ☒NcheckY (what is this?)  (verify)

19-Norandrosterone, also known as5α-estran-3α-ol-17-one, is ametabolite ofnandrolone (19-nortestosterone) andbolandione (19-norandrostenedione) that is formed by5α-reductase. It is on the list of substances prohibited by theWorld Anti-Doping Agency since it is a detectable metabolite of nandrolone, ananabolic-androgenic steroid (AAS).[1] Consumption ofandrostendione products contaminated with traces of bolandione may also result in testing positive for nandrolone.[2]

Traces of 19-norandrosterone may be naturally present in humanurine. An experiment conducted on athletes showed that after a prolonged intense effort, the 19-norandrosterone concentration can be increased by a factor varying between 2 and 4,[3] but another study failed to replicate the result.[4] Concentration also increases in the urine of female athletes duringmenstruation.[5] The consumption of edible parts of a non-castrated pig, containing 19-nortestosterone, has been shown to result in the excretion of 19-norandrosterone in the following hours, so athletes should prudently avoid meals composed of pigoffal in the hours preceding doping tests.[6] Consumption of boar meat, liver, kidneys and heart also increased 19-norandrosterone output.[7]

See also

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References

[edit]
  1. ^"THE 2007 PROHIBITED LIST INTERNATIONAL STANDARD"(PDF).The World Anti-Doping Code.World Anti-Doping Agency. Archived fromthe original(PDF) on 10 April 2009. Retrieved2009-05-14.
  2. ^Catlin DH, Leder BZ, Ahrens B, Starcevic B, Hatton CK, Green GA, Finkelstein JS (2000)."Trace contamination of over-the-counter androstenedione and positive urine test results for a nandrolone metabolite".JAMA.284 (20):2618–21.doi:10.1001/jama.284.20.2618.PMID 11086369. Retrieved29 December 2008.
  3. ^Le Bizec B, Monteau F, Gaudin I, André F (February 1999). "Evidence for the presence of endogenous 19-norandrosterone in human urine".J. Chromatogr. B.723 (1–2):157–72.doi:10.1016/S0378-4347(98)00541-6.PMID 10080643.
  4. ^Schmitt N, Flament MM, Goubault C, Legros P, Grenier-Loustalot MF, Denjean A (September 2002)."Nandrolone excretion is not increased by exhaustive exercise in trained athletes".Med Sci Sports Exerc.34 (9):1436–9.doi:10.1097/00005768-200209000-00006.PMID 12218735.
  5. ^Van Eenoo P, Delbeke FT, de Jong FH, De Backer P (October 2001). "Endogenous origin of norandrosterone in female urine: indirect evidence for the production of 19-norsteroids as by-products in the conversion from androgen to estrogen".J. Steroid Biochem. Mol. Biol.78 (4):351–7.doi:10.1016/S0960-0760(01)00112-1.PMID 11717005.S2CID 19065089.
  6. ^Ayotte C (July 2006)."Significance of 19-norandrosterone in athletes' urine samples".Br J Sports Med.40 (Suppl 1): i25–9.doi:10.1136/bjsm.2006.028027.PMC 2657496.PMID 16799098.
  7. ^Le Bizec B, Gaudin I, Monteau F, Andre F, Impens S, De Wasch K, De Brabander H (2000). "Consequence of boar edible tissue consumption on urinary profiles of nandrolone metabolites. I. Mass spectrometric detection and quantification of 19-norandrosterone and 19-noretiocholanolone in human urine".Rapid Commun. Mass Spectrom.14 (12):1058–65.doi:10.1002/1097-0231(20000630)14:12<1058::AID-RCM991>3.0.CO;2-7.PMID 10861987.

External links

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ARTooltip Androgen receptor
Agonists
SARMsTooltip Selective androgen receptor modulator
Antagonists
GPRC6A
Agonists
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